US4220711A - Silver halide color photographic light-sensitive element - Google Patents

Silver halide color photographic light-sensitive element Download PDF

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Publication number
US4220711A
US4220711A US06/019,019 US1901979A US4220711A US 4220711 A US4220711 A US 4220711A US 1901979 A US1901979 A US 1901979A US 4220711 A US4220711 A US 4220711A
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silver halide
photographic light
interlayer
sensitive element
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US06/019,019
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Kotaro Nakamura
Akio Mitsui
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Fujifilm Holdings Corp
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Fuji Photo Film Co Ltd
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
    • G03C1/815—Photosensitive materials characterised by the base or auxiliary layers characterised by means for filtering or absorbing ultraviolet light, e.g. optical bleaching
    • G03C1/8155—Organic compounds therefor

Definitions

  • the present invention relates to a method of preventing color stain from occurring in a color photographic light sensitive element when the sensitive element is exposed to light (such stain is hereafter referred to as "light stain").
  • an object of the present invention is to provide a method of suppressing the occurrence of light stain to a greater extent than has been possible conventionally.
  • Another object of the present invention is to provide a color photographic light sensitive element having light stain reduced to a greater extent than conventional materials.
  • a silver halide color photographic light-sensitive element comprising a support having thereon at least one silver halide emulsion layer and at least one layer comprising a solution of at least one hydrophobic compound represented by the general formula (I) dissolved in an alkyl phosphoric acid ester represented by the general formula (III) dispersed in a gelatin-containing hydrophilic colloid in which no dye-forming agents are contained.
  • this layer is referred to as the interlayer of the present invention.
  • the hydrophobic compound is a compound of the formula (I) ##STR3## wherein R 1 , R 2 , R 3 , R 4 and R 5 may be the same or different and each represents a hydrogen atom, a halogen atom, a nitro group, a hydroxyl group, an alkyl group, an alkenyl group, an aryl group, an alkoxy group, an acyloxy group, an aryloxy group, an alkylthio group, an arylthio group, an aralkylthio group, a mono or dialkylamino group, an acylamino group, or a 5- or 6-membered heterocyclic ring containing an oxygen or a nitrogen atom and further, R 4 and R 5 may combine to form a 5- or 6-membered aromatic carbocyclic ring.
  • R 6 , R 7 and R 8 each represents a branched chain alkyl group having 8 or more carbon atoms where the total number
  • the interlayer of the present invention may be provided at any position in a multilayer arrangement of a color photographic light sensitive element, but it is preferred to provide the interlayer of the present invention at a position adjacent to a magenta dye image-forming layer.
  • halogen atoms represented by R 1 , R 2 , R 3 , R 4 or R 5 in the general formula (I) include a chlorine atom, a bromine atom, an iodine atom and a fluorine atom.
  • the alkyl groups represented by R 1 , R 2 , R 3 , R 4 or R 5 in the general formula (I) may be straight chain, branched chain or cyclic, substituted or unsubstituted and contain 1 to 30 carbon atoms such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an aminopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, a chlorobutyl group, an n-amyl group, an iso-amyl group, a hexyl group, an octyl group, a nonyl group, a stearylamindobutyl group, a decyl group, a dodecyl group, a pentadecyl group, a hexadecyl group, a cyclohexyl group, a benzyl
  • alkenyl groups represented by R 1 , R 2 , R 3 , R 4 or R 5 in the general formula (I) include straight chain or branched chain alkenyl groups having 1 to 30 carbon atoms such as a vinyl group, an allyl group, a methallyl group, a dodecenyl group, a tridecenyl group, a tetradecenyl group, an octadecenyl group and the like.
  • aryl groups represented by R 1 , R 2 , R 3 , R 4 or R 5 in the general formula (I) include a mono- or bi-cyclic, substituted or unsubstituted aryl groups having 6 to 32 carbon atoms such as a phenyl group, a 4-methylphenyl group, a 4-ethoxyphenyl group, a 2-hexyloxyphenyl group, a 3-hexyloxyphenyl group and the like.
  • alkoxy groups represented by R 1 , R 2 , R 3 , R 4 or R 5 in the general formula (I) include substituted or unsubstituted alkoxy groups containing 1 to 30 carbon atoms in the alkyl moiety such as methoxy group, an ethoxy group, a propoxy group, a butoxy group, a chlorobutoxy group, a decyloxy group, a diaminophenoxy group, a pentadecyloxy group, an octadecyloxy group and the like.
  • acyloxy groups represented by R 1 , R 2 , R 3 , R 4 or R 5 in the general formula (I) include acyloxy groups derived from aliphatic carboxylic acids and containing 1 to 30 total carbon atoms such as a carbomethoxy group, a carbobutoxy group, a carbohexyloxy group, a carbopentadecyloxy group and the like.
  • aryloxy groups represented by R 1 , R 2 , R 3 , R 4 or R 5 in the general formula (I) include mono- or bi-cyclic aryloxy groups having 6 to 32 carbon atoms such as a phenoxy group, a 4-methylphenoxy group, a 2-propylphenoxy group, a 3-amylphenoxy group and the like.
  • alkylthio groups represented by R 1 , R 2 , R 3 , R 4 or R 5 in the general formula (I) include alkylthio groups having 1 to 30 carbon atoms such as a methylthio group, an ethylthio group, a tert-butylthio group, a tert-octylthio group and the like.
  • Examples of aralkylthio groups represented by R 1 , R 2 , R 3 , R 4 or R 5 in the general formula (I) include mono- or bi-cyclic aralkylthio groups having 7 to 30 carbon atoms such as a benzylthio group and the like.
  • arylthio groups represented by R 1 , R 2 , R 3 , R 4 or R 5 in the general formula (I) include substituted and unsubstituted arylthio groups having 6 to 32 carbon atoms such as a phenylthio group a methylphenylthio group, an ethylphenylthio group, a methoxyphenylthio group, an ethoxyphenylthio group, a naphthylthio group and the like.
  • Examples of mono- or di-alkylamino groups represented by R 1 , R 2 , R 3 , R 4 or R 5 in the general formula (I) include mono- or di-alkylamino groups having 1 to 30 carbon atoms such as an N-ethylamino group, an N-tert-octylamino group, an N,N-diethylamino group, an N,N-di-tert-butylamino group and the like.
  • acylamino groups represented by R 1 , R 2 , R 3 , R 4 or R 5 in the general formula (I) include acylamino groups having 1 to 30 carbon atoms such as an acetylamino group, a benzoylamino group, a methanesulfonylamino group and the like.
  • Examples of 5- or 6-membered, oxygen- or nitrogen-containing heterocyclic rings represented by R 1 , R 2 , R 3 , R 4 or R 5 in the formula (I) include a piperidine group, a morpholine group, a pyrrolioline group, a piperazine group and the like.
  • Examples of 5- or 6-membered carbocyclic rings formed by the combination of R 4 and R 5 in the general form (I) include a phenyl ring, a cyclohexyl ring and the like.
  • substituents represented by R 1 to R 5 contain preferably 5 to 36 carbon atoms in the sum total and further, each of alkyl groups represented by some of the substituents desirably contains 1 to 18 carbon atoms.
  • Particularly preferable compounds are those in which R 4 is a halogen atom in the general formula (II).
  • R 7 and R 8 in the general formula (III) each has preferably 8 to 10 carbon atoms and more preferably, each has 9 carbon atoms.
  • R 6 , R 7 and R 8 each includes ##STR6##
  • the compounds represented by the general formula (III) which may be employed in the present invention can be prepared by the reaction of phosphorus oxychloride with alcohols, as described in J. R. van Wazer, Phosphorus and Its Compounds, volume 2, page 1221, in such a reaction, a base may be used in order to remove hydrogen chloride formed as a by-product. Examples of syntheses of these compounds are illustrated specifically below.
  • a suitable amount of the compound represented by the general formula (I) to be added to the interlayer is about 0.1 to about 6 g/m 2 and preferably 0.2 to 1.8 g/m 2
  • a suitable amount of the compound represented by the general formula (III) to be added to the interlayer is about 0.01 to 1 cc/m 2 and preferably 0.1 to 0.5 cc/m 2 .
  • the compounds represented by the general formula (I) may be employed individually or in combinations thereof.
  • the present invention is characterized by the use of the compound represented by the general formula (III) as the solvent for 2-(2'-hydroxyphenyl)-benzotriazole compounds which are ultraviolet ray absorbing agents.
  • An appropriate amount of the compound represented by the formula (I) to be dissolved in the compound represented by the formula (III) is about 0.1 to about 15 g/cc and preferably 1 to 10 g/cc.
  • 3,253,921 are used as the solvents for dissolving 2-(2'-hydroxyphenyl)-benzotriazole, the objects of the present invention can not be attained at all even in the case that the ultraviolet ray absorbing agent of the present invention is added to a certain layer not containing any dye-forming agents.
  • the occurrence of the light stain in the color sensitive element can be reduced to a very low level only when the compound represented by the general formula (III) is used as a solvent for the ultraviolet ray absorbing agent employed in the present invention and the solution is added to a layer not containing any dye-forming agents.
  • the interlayer of the present invention may contain as a color mixing inhibitor such as a hydroquinone derivative, an aminophenol derivative, a gallic acid derivative, an ascorbic acid derivative or the like.
  • a color mixing inhibitor such as a hydroquinone derivative, an aminophenol derivative, a gallic acid derivative, an ascorbic acid derivative or the like.
  • Specific examples of these color mixing inhibitors are described in U.S. Pat. Nos. 2,360,290; 2,336,327; 2,403,721; 2,418,613; 2,675,314; 2,701,197; 2,704,713; 2,728,659; 2,732,300 and 2,735,765: Japanese Patent Applications OPI 92,988/75; 92,989/75; 93,928/75 and 110,337/75: Japanese Patent Publication 23,813/75: and so on.
  • An appropriate addition amount of the color mixing inhibitor ranges from 0.01 g/m 2 to 0.5 g/m 2 .
  • a suitable amount of gelatin coated in the interlayer is about 0.1 to about 3.0 g/m 2 , preferably 0.2 to 1.5 g/m 2 .
  • the interlayer of the present invention may contain a wide variety of known surface active agents for various purposes. For instance, to use as a coating aid, to increase antistatic effect, to improve slipping property, to facilitate formation of the emulsified dispersion, to prevent adhesion, to improve photographic characteristics (e.g., development acceleration, image contrast, sensitization, etc.) and so on.
  • surface active agents for various purposes. For instance, to use as a coating aid, to increase antistatic effect, to improve slipping property, to facilitate formation of the emulsified dispersion, to prevent adhesion, to improve photographic characteristics (e.g., development acceleration, image contrast, sensitization, etc.) and so on.
  • nonionic surface active agents include saponin (e.g., steroid system), alkyleneoxide derivatives (e.g., polyethylene glycol, polyethylene glycol-polypropylene glycol condensate, polyethylene glycol alkyl or alkylaryl ether, polyethylene glycol esters, polyethylene glycol sorbitan esters, polyalkylene glycol alkylamines or polyalkylene glycol alkylamides, polyethyleneoxide adducts of silicones and the like), glycidol derivatives (such as alkenylsuccinic acid polyglyceride, alkylphenol polyglyceride and the like), fatty acid esters of polyhydric alcohols, alkyl esters of sugar, urethanes or ethers of sugar and so on; anionic surface active agents containing acid groups such as a carboxy group, a sulfo group, a phospho group, a sulfate group, a phosphate group and the
  • a hydrophilic colloidal solution for making the interlayer of the present invention may contain water soluble dyes as filter dyes or for various other purposes (it is emphasized, however, that the interlayer does not contain a dye image forming material); for instance, anti-irradiation and others.
  • dyes include oxonol dyes, hemioxonol dyes, styryl dyes, merocyanine dyes, cyanine dyes and azo dyes. Of these dyes, oxonol dyes, hemioxonol dyes and merocyanine dyes are preferred.
  • dyes employable in the present invention include those which are described in British Patents 584,609 and 1,117,429: Japanese Patent Applications (OPI) Nos. 85,130/73; 99,620/74 and 114,420/74; and U.S. Pat. Nos. 2,274,782; 2,533,472; 2,956,879; 3,148,187; 3,177,078; 3,247,127; 3,540,887; 3,575,704; 3,653,905 and 3,718,472.
  • the sensitive element prepared in accordance with the method of the present invention on the occasion that dyes and ultraviolet ray absorbing agents are incorporated in the hydrophilic colloidal layer(s), they may be mordanted with cationic polymers.
  • specific polymers described in British Pat. No. 685,475; U.S. Pat. Nos. 2,675,316; 2,839,401; 2,882,156; 3,048,487; 3,184,309 and 3,445,231; Germany Patent Application (OLS) No. 1,914,362; Japanese Patent Applications (OPI) Nos. 47,624/75 and 71,332/75; and so on can be employed.
  • Photographic emulsion layers of the photographic light sensitive element prepared in accordance with the method of the present invention contain color image forming couplers; that is to say, compounds capable of producing dyes by reacting with oxidation products of aromatic amine (usually primary amine) developing agents. Couplers having hydrophobic non-diffusible groups called ballast groups in their molecules are preferred.
  • the couplers may be four equivalent or two equivalent with respect to the silver ion.
  • Such couplers may include colored couplers possessing color correction effect or couplers releasing development inhibitors with the progress of development (so-called DIR couplers).
  • the couplers may include such couplers that the products of a coupling reaction may be colorless.
  • yellow color-forming couplers known open chain ketomethylene series couplers can be employed. Of these couplers, benzoylacetoanilide compounds and pivaloylacetoanilide compounds are used to advantage. Specific examples of yellow color-forming couplers employable herein include those which are described in U.S. Pat. Nos. 2,875,057; 3,265,506; 3,408,194; 3,551,155; 3,582,322; 3,725,072 and 3,891,445; German Pat. No. 1,547,868; German Patent Application (OLS) Nos. 2,219,917; 2,261,361 and 2,414,006 British Pat. No. 1,425,020, Japanese Pat. No.
  • magenta color-forming couplers pyrazolone compounds indazolone compounds cyanoacetyl compounds and the like can be employed. Of these compounds, pyrazolone compounds are of greater advantage.
  • suitable magenta color forming couplers include those which are described in U.S. Pat. Nos. 2,600,788; 2,983,608; 3,062,653; 3,127,269; 3,311,476; 3,419,391; 3,519,429; 3,558,319; 3,582,322; 3,615,506; 3,834,908 and 3,891,445; German Pat. No. 1,810,464; German Patent Application (OLS) Nos.
  • cyan color-forming couplers phenol compounds, naphthol compounds and the like can be employed. Specific examples thereof include those which are described in U.S. Pat. Nos. 2,639,929; 2,434,272; 2,474,293; 2,521,908; 2,895,826; 3,034,892; 3,311,476; 3,458,315; 3,476,563; 3,583,971; 3,591,383; 3,767,411 and 4,004,929; German Patent Application (OLS) Nos. 2,414,830 and 2,454,329; and Japanese Patent Application (OPI) Nos. 59,838/73; 26,034/76; 5,055/73 and 146,828/76.
  • DIR couplers those which are described in, for example, U.S. Pat. Nos. 3,227,554; 3,617,291; 3,701,783; 3,790,384 and 3,632,345; German Patent Application (OLS) Nos. 2,414,006; 2,454,301 and 2,454,329; British Pat. No. 953,454; Japanese Patent Application (OPI) Nos. 69,624/77 and 122,335/74 and Japanese Pat. No. 16,141/76 can be employed.
  • Such compounds which release development inhibitors with the progress of a developmental reaction may be contained in the sensitive element, and they include those which are described in, for example, U.S. Pat. Nos. 3,297,445 and 3,379,529; and German Patent Application (OLS) No. 2,417,914.
  • two or more couplers may be contained in the same layer, or the same coupler may be contained in two or more different layers.
  • the couplers are first dissolved in certain high boiling point organic solvents with specific examples include phthalic acid alkyl esters (e.g., dibutyl phthalate, dioctyl phthalate, etc.), phosphoric acid esters (e.g., diphenyl phosphate, triphenyl phosphate, tricresyl phosphate, dioctylbutyl phosphate, etc.), citric acid esters (e.g., tributyl acetylcitrate, etc.), benzoic acid esters (e.g., octyl benzoate, etc.), alkylamides (e.g., diethyllauryl amide, etc.) and the compounds represented by the general formula (III) of the present invention (e.g.,
  • organic solvents with specific examples including lower alkyl acetates such as ethyl acetate, butyl acetate, etc., ethyl propionate, sec-butyl alcohol, methyl isobutyl ketone, ⁇ -ethoxyethyl acetate, methyl cellosolve acetate; and the like and then, the resulting solutions are dispersed into hydrophilic colloids.
  • the high boiling point organic solvents and the low boiling point organic solvents may be also employed in a mixed form.
  • a coupler has acid group(s) such as a carboxylic acid group, a sulfonic acid group or the like
  • the coupler is introduced into a hydrophilic colloid in a form of an alkaline aqueous solution.
  • couplers are generally added in amounts of about 2 ⁇ 10 -3 to 5 ⁇ 10 -1 mole per mole of silver in the emulsion layer and preferably, in amounts of 1 ⁇ 10 -2 to 5 ⁇ 10 -1 mole per mole of silver therein.
  • photographic emulsion layers and others are coated on (or over) a commonly used flexible support such as a plastic film, paper, cloth or the like or a commonly used rigid support such as glass, earthenware, metal or the like.
  • flexible supports include films made of semisynthetic or synthetic high polymers, such as cellulose nitrate, cellulose acetate, cellulose acetate butyrate, polystyrene, polyvinyl chloride, polyethylene terephthalate, polycarbonate, etc.; and paper coated or laminated with a baryta layer or an ⁇ -olefin polymer (e.g., polyethylene, polypropylene, ethylene-butene copolymer or the like).
  • the support may be colored with a certain dye or a certain pigment. For the purpose of light shielding, the support may be also colored black.
  • the surface of the support is generally subjected to a subbing treatment in order to enhance the adhesion power between the support and a photographic emulsion layer to be provided thereon. Further, the surface of the support may receive a corona discharge, a ultraviolet irradiation, a flame spraying or like treatment.
  • a color photographic light-sensitive element was prepared by coating, on a paper support both sides of which were laminated with polyethylene films, in sequence the first layer (corresponding to the lowest layer) to the sixth layer (corresponding to the topmost layer), as described with respect to their respective functions and compositions in the following Table 3.
  • Each of samples prepared was labeled as shown in Table 1 depending upon the solvent used for dissolving the ultraviolet ray absorbent contained in the fourth layer.
  • color photographic light-sensitive element were prepared by coating on a paper support both side of which were laminated with polyethylene films in sequence three layers which were the same as the third layer, the fourth layer and the sixth layer used in Example 1 except that the kind and amount of ultraviolet ray absorbing agent as well as the kind of coupler solvent were changed as shown in Table 5.
  • color sensitive elements prepared were labeled as shown in Table 5.
  • Example 6 Each of these samples was exposed to light and development-processed in the same manner as in Example 1. Each of the thus obtained samples was exposed to light generated from a xenone lamp with the illumination intensity of 200,000 luxes and the density of the white areas of each sample changed by the stain produced therein, as set forth in Table 6.

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  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
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US06/019,019 1978-03-09 1979-03-08 Silver halide color photographic light-sensitive element Expired - Lifetime US4220711A (en)

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JP2683478A JPS54119235A (en) 1978-03-09 1978-03-09 Silver halide color photographic material
JP53-26834 1978-03-09

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WO1981001473A1 (en) * 1979-11-09 1981-05-28 Minnesota Mining & Mfg Uv-absorbing compounds and photographic elements containing them
US4353979A (en) * 1979-07-25 1982-10-12 Konishiroku Photo Industry Co., Ltd. Light-sensitive silver halide photographic materials
US4518686A (en) * 1982-06-05 1985-05-21 Konishiroku Photo Industry Co., Ltd. Color photographic light-sensitive material containing UV filter compounds
US4540656A (en) * 1982-06-01 1985-09-10 Konishiroku Photo Industry Co., Ltd. Color photographic light-sensitive material
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US5573900A (en) * 1994-05-20 1996-11-12 Fuji Photo Film Co., Ltd. Dispersion method of hydrophobic, photographically useful compound
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DE3367983D1 (en) * 1982-06-01 1987-01-15 Konishiroku Photo Ind A color photographic light-sensitive material
JPS58211148A (ja) * 1982-06-02 1983-12-08 Konishiroku Photo Ind Co Ltd カラ−写真感光材料
US4526853A (en) * 1982-10-15 1985-07-02 Konishiroku Photo Industry Co., Ltd. Method of providing an increased brightening effect and silver halide photographic material having increased brightening effect
JPS59215378A (ja) * 1983-05-21 1984-12-05 Konishiroku Photo Ind Co Ltd 乳化分散物
JPH07119938B2 (ja) * 1986-08-01 1995-12-20 コニカ株式会社 迅速処理に適したハロゲン化銀写真感光材料
JPS63187240A (ja) * 1987-01-29 1988-08-02 Konica Corp ハロゲン化銀写真感光材料

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US4353979A (en) * 1979-07-25 1982-10-12 Konishiroku Photo Industry Co., Ltd. Light-sensitive silver halide photographic materials
WO1981001473A1 (en) * 1979-11-09 1981-05-28 Minnesota Mining & Mfg Uv-absorbing compounds and photographic elements containing them
US4540656A (en) * 1982-06-01 1985-09-10 Konishiroku Photo Industry Co., Ltd. Color photographic light-sensitive material
USRE37693E1 (en) * 1982-06-05 2002-05-07 Konishiroku Photo Industry Co., Ltd. Color photographic light-sensitive material containing UV filter compounds
US4518686A (en) * 1982-06-05 1985-05-21 Konishiroku Photo Industry Co., Ltd. Color photographic light-sensitive material containing UV filter compounds
US5298380A (en) * 1991-09-05 1994-03-29 Ciba-Geigy Corporation Photographic material which contains a UV absober
US5204231A (en) * 1992-03-31 1993-04-20 Konica Imaging, U.S.A., Inc. White safelight handleable photographic film containing a filter dye layer
US5593818A (en) * 1993-06-22 1997-01-14 Fuji Photo Film Co., Ltd. Silver halide photographic material
US5573900A (en) * 1994-05-20 1996-11-12 Fuji Photo Film Co., Ltd. Dispersion method of hydrophobic, photographically useful compound
US5585228A (en) * 1994-11-30 1996-12-17 Eastman Kodak Company Benzotriazole based UV absorbing compounds and photographic elements containing them
US5731137A (en) * 1995-08-18 1998-03-24 Fuji Photo Film Co., Ltd. Emulsified dispersion and silver halide color photographic light-sensitive material containing the same
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Also Published As

Publication number Publication date
DE2909021A1 (de) 1979-09-20
GB2017325A (en) 1979-10-03
JPS54119235A (en) 1979-09-17
DE2909021C2 (enrdf_load_stackoverflow) 1989-05-24
GB2017325B (en) 1982-06-23
JPS6148147B2 (enrdf_load_stackoverflow) 1986-10-22

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